(S)-Ethyl 3-cyano-3-hydroxypropanoate

Base Information

• Chemical Name: (S)-Ethyl 3-cyano-3-hydroxypropanoate
• CAS No.: 132839-91-9
• Molecular Formula: C6H9NO3
• Molecular Weight: 143.14056
• DSSTox Substance ID: DTXSID60455299
• Wikidata: Q82277243
• Mol file: 132839-91-9.mol

Synonyms:(S)-Ethyl 3-cyano-3-hydroxypropanoate;132839-91-9;ETHYL (3S)-3-CYANO-3-HYDROXYPROPANOATE;(S)-3-CYANO-3-HYDROXY-PROPIONIC ACID ETHYL ESTER;DTXSID60455299;(S)-Ethyl3-cyano-3-hydroxypropanoate;AKOS006329380;A888250

Chemical Property of (S)-Ethyl 3-cyano-3-hydroxypropanoate

Chemical Property:

• PSA: 70.32000
• LogP: -0.17592
• Storage Temp.: 2-8°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99%min ^*data from raw suppliers

(S)-Ethyl3-cyano-3-hydroxypropanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C#N)O
• Isomeric SMILES: CCOC(=O)C[C@@H](C#N)O

Technology Process of (S)-Ethyl 3-cyano-3-hydroxypropanoate

There total 3 articles about (S)-Ethyl 3-cyano-3-hydroxypropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trimethylsilyl cyanide (7677-24-9) + 3-oxo-propionic acid ethyl ester (34780-29-5) → (+/-)-ethyl 3-cyano-3-hydroxypropionate (132839-91-9)

Guidance literature:

With sodium hydroxide; acetic acid; In ethanol; water;

DOI:10.1016/S0957-4166(00)82379-4

Reference yield: 54.0%

3-oxo-propionic acid ethyl ester (34780-29-5) + potassium cyanide (151-50-8) → (+/-)-ethyl 3-cyano-3-hydroxypropionate (132839-91-9)

Guidance literature:

With acetic acid; In ethanol; water; for 0.25h; pH 5.4;

DOI:10.1016/S0957-4166(00)82379-4

Reference yield:

ethyl 3,3-diethoxypropanoate (10601-80-6) → (+/-)-ethyl 3-cyano-3-hydroxypropionate (132839-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / trifluoroacetic acid, water / CH₂Cl₂ / 2 h / Ambient temperature

2: 98 percent / 1 N sodium acetate buffer, pH 5.4 / ethanol; H₂O / 1 h / Ambient temperature

With sodium acetate buffer; water; trifluoroacetic acid; In ethanol; dichloromethane; water;

DOI:10.1016/S0957-4166(00)80128-7

upstream raw materials:

trimethylsilyl cyanide

3-oxo-propionic acid ethyl ester

potassium cyanide

ethyl 3,3-diethoxypropanoate

Downstream raw materials:

(+/-)-ethyl O-acetyl-3-cyano-3-hydroxypropionate

Refernces

• 1、 Lu,Miet,Kunesch,Poisson. "A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution". . p. 893 - 902. Retrieved 2007/10/02.